Two equivalents of this functional group react in a cascade of two consecutive rearrangements first reported by Banert. A diphenylphosphoryl reagent of this functionality is useful for forming urethanes when the Schmidt reaction fails. An acyl example of this functional group participates in a reaction that is analogous to the Wolff rearrangement; an isocyanate results from that reaction, named for Curtius. This functional group can react with an alkyne in a 1,3-dipolar cycloaddition to form a 1,2,3-triazole; that reaction is a type of Huisgen cyclization important to click chemistry. Students will generally first encounter blast shields and 
Two equivalents of this functional group react in a cascade of two consecutive rearrangements first reported by Banert. A diphenylphosphoryl reagent of this functionality is useful for forming urethanes when the Schmidt reaction fails. An acyl example of this functional group participates in a reaction that is analogous to the Wolff rearrangement; an isocyanate results from that reaction, named for Curtius. This functional group can react with an alkyne in a 1,3-dipolar cycloaddition to form a 1,2,3-triazole; that reaction is a type of Huisgen cyclization important to click chemistry. Students will generally first encounter blast shields and double-gloving in working with this functional group's sodium salt, which is used in air bags because it releases nitrogen gas when heated. For 10 points, name this functional group, which consists of three consecutive nitrogen atoms connected by double bonds.
Two equivalents of this functional group react in a cascade of two consecutive rearrangements first reported by Banert.
{azide}